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Efficient Syntheses of Vitamin K Chain-Shortened Acid Metabolites.

ABSTRACT: Vitamin K sequentially undergoes ?-oxidation followed by successive rounds of ?-oxidation to ultimately produce two chain-shortened carboxylic acid metabolites, vitamin K acid 1 and vitamin K acid 2. Two facile syntheses of these acid metabolites are described, each starting from commercially available menadione-cyclopentadiene adduct 3. Vitamin K acid 1 was synthesized in five steps via alkylation with a geranyl halide followed by subsequent oxidation reactions, while fully retaining the trans configuration of the side chain 2',3'-double bond. Vitamin K acid 2 was synthesized in 5 steps from 3via alkylation with dimethylallyl chloride and subsequent oxidation reactions.

SUBMITTER: Teitelbaum AM

PROVIDER: S-EPMC4798747 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Efficient Syntheses of Vitamin K Chain-Shortened Acid Metabolites.

Teitelbaum Aaron M AM Scian Michele M Nelson Wendel L WL Rettie Allan E AE

Synthesis 20150401 7

Vitamin K sequentially undergoes ω-oxidation followed by successive rounds of β-oxidation to ultimately produce two chain-shortened carboxylic acid metabolites, vitamin K acid 1 and vitamin K acid 2. Two facile syntheses of these acid metabolites are described, each starting from commercially available menadione-cyclopentadiene adduct <b>3</b>. Vitamin K acid 1 was synthesized in five steps <i>via</i> alkylation with a geranyl halide followed by subsequent oxidation reactions, while fully retain ...[more]

PMID: 27003951

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